277744-76-0Relevant articles and documents
Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis
Kang, Bubwoong,Wang, Yinli,Kuwano, Satoru,Yamaoka, Yousuke,Takasu, Kiyosei,Yamada, Ken-Ichi
supporting information, p. 4469 - 4472 (2017/04/26)
A highly site-selective N-heterocyclic carbene (NHC)-catalyzed benzoin-type cyclization of unsymmetrical dialdoses is developed to enable a divergent cyclitol synthesis. The choice of chiral NHCs and protecting groups affects the site-selectivity. The resulting inososes are converted into epi-, muco- and myo-inositols, and their chiral protected derivatives are formed in good yields.
Ruthenium carbene complexes with imidazol-2-ylidene ligands: Syntheses of conduritol derivatives reveals superior RCM activity
Ackermann, Lutz,El Tom, David,Fürstner, Alois
, p. 2195 - 2202 (2007/10/03)
Syntheses of conduritol A, E and F derivatives are described using galactitol, D-mannitol and D-glucitol, respectively, as the starting materials. The key steps of this approach comprise a Tebbe olefination reaction for the preparation of dienes 15, 21 and 27 followed by ring closing metathesis (RCM) for the formation of the polyhydroxylated cyclohexene rings of the targets. A comparative study shows that the latter transformation is best achieved with catalytic amounts of ruthenium carbene complex 3a bearing one PCy3 and one 2,3-dihydro-1H-imidazol-2-ylidene ligand in its coordination sphere. (C) 2000 Elsevier Science Ltd.